Introverted CB[N] Compounds

a technology of cucurbituril and compound, applied in the field of introverted cucurbituril cbn compounds, can solve the problems of complex and achieve the effect of reducing the complexity and unreliability of conventional preparatory methods

Inactive Publication Date: 2010-01-14
UNIV OF MARYLAND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Later synthetic efforts to prepare CB[n] compounds demonstrated the complexity and unreliability of conventional preparatory methods.

Method used

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  • Introverted CB[N] Compounds
  • Introverted CB[N] Compounds
  • Introverted CB[N] Compounds

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0108]

Synthesis:

[0109]Powered glycoluril (795 g, 5.59 mol) and powered paraformaldehyde (354 g, 11.20 mmol) were mixed thoroughly. An ice-cold concentrated HC1 solution (1130 mL) was added gradually while stirring with a large glass rod. After the addition of a ˜100 m / , stirring was no longer possible and solidification was observed and an exotherm was observed. The heterogenous mixture was gradually heated to 80□ (2.5 h) and maintained at that temperature for 2.5 hours until all the solid had dissolved. The homogenous red solution was heated to 100° C. for 14 hours. After cooling to room temperature, the purification process was begun.

Purification:

[0110]Initial processing: The reaction mixture which contains a large amount of solid was evaporated as to a minimum volume. This slurry was poured into water (2.5 L). The solid was collected by filtration to give the first crop (Crop I) (contains: CB[6], CB[7], CB[8], some introverted CB[6], and some CB[5]@CB[10]). The filtrate was evapo...

example 2

[0124]

[0125]i-CB[6] and i-CB[7] were synthesized using the procedures described above. Each were characterized by 1H NMR spectroscopy and x-ray crystallography, after separation by gel permeation chromatography.

[0126]The i-CB[n] are detected by 1H NMR spectroscopy in CB[n] reaction mixtures produced from the reaction between glycoluril and formaldehyde in acidic media. When p-xylylenediammonium ion (1) is added as a probe to a mixture of CB[n], each different CB[n]⊙1 and i-CB[n]1 exhibits a single diagnostic aromatic resonance (FIG. 4a, 6.9-6.4 ppm). i-CB[6] and i-CB[7] were isolated in 2.0% and 0.4% yields, respectively, in pure form either by gel permeation chromatography (Superdex 30, 0.15 M NH4HCO3) or by fractional crystallization (18% aq. HCl) followed by selective complexation (i-CB[6]: +H3N(CH2)6NH3+, 2) to remove other CB[n]. The structures of i-CB[6] and i-CB[7] (FIGS. 4b and 4c) were unequivocally established by 2D NMR spectroscopy.

[0127]The methane resonances for the in...

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Abstract

Inverted cucurbituril compounds having at least one pair of hydrogen atoms protruding into an internal molecular cavity thereof.

Description

CROSS REFERENCE TO RELATED CASES[0001]This application claims the benefit of U.S. Provisional Application Ser. Nos. 60 / 701,732, filed Jul. 22, 2005, and 60 / 736,991, filed Nov. 15, 2005, which are both incorporated by reference herein in their entirety. This application also incorporates pending U.S. application Ser. No. 10 / 933,538, herein in the entirety.STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH[0002]The work leading up to the invention described herein was funded, at least in part, by NIH R01GM61854. Thus, the U.S. Government may have certain rights thereto under 35 U.S.C. 203 et seq.BACKGROUND OF THE INVENTION[0003]1. Field of the Invention[0004]The present invention relates to introverted cucurbituril CB[n] compounds and / or derivatives, and methods of making and using the same as well as to an improved synthesis of higher cucurbituril compounds.[0005]2. Description of the Background[0006]Cucurbituril (CB[n]) compounds are macrocyclic compounds containing glycouril repeat u...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor ISAACS, LYLE DAVIDLIU, SIMINKIM, KIMOONPARK, SANG-KYUKO, YOUNG HOKIM, HYUNUKKIM, YOUNGKOOKSELVAPALAM, NARAYANAN
Owner UNIV OF MARYLAND
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